The gray area of sexual violations generally refers to ambiguous sexual experiences that are not readily distinguishable from rape or sex. Such experiences are describable as ambiguous or complex in a way that, to some, seems to defy existent categories of sexual experiences. This leads some feminists to approach the gray area as a puzzle that must be resolved either by understanding it as a new category, or by upholding existing rape categorization. Rather than dispelling the gray-area ambiguity by resolving conceptual puzzles, I assign the gray-area ambiguity a positive analytical role by attending to it in a historical and dialectical light. By tracing histories of feminist antirape discourse, I elaborate a way of understanding the “gray area” of sexual violations, articulating it as a historical condition affecting the interpretive possibilities of our sexual experiences. Such an approach underscores the potential of the gray area to inaugurate feminist critique in virtue of its status as a historically specific yet ambiguous horizon where our experiences can contradictorily seem not-like rape, but not-like sex.